Gina's Dares

The thought of sharing a hotel room with Ron didn’t bother me at all. In fact, the idea that it is unusual at all only crossed my mind because of the reaction of the other girls at work. By their reactions, you’d think that I was traveling out of town for some sort of tryst with a tall, dark, and handsome stranger rather than attending a convention with an old friend.

“Gina, you’re gonna get you some this weekend, girl,” Becca had said, laughing.

The more I protested that we were just trying to save money by sharing a room, the more they teased me about my supposed impending liaison. By the time that I left work on Wednesday to make the long drive, I was wondering if the money saved was worth it for more reasons than one. Logically, though, I knew that it was.

Having just graduated and started life in the real world, I was swimming in expenses. Coming up with the deposit on my apartment had tapped out my bank account, and there always seemed to be more expenses than I expected to eat up each paycheck. Staying in a hotel that was a quite a way from the actual convention facilities cut the cost in half and sharing the room knocked off another half of that.

Try as I might, I couldn’t come up with any big reasons against the idea. I didn’t even have to modify my sleep attire much as my full pj’s were more than modest enough to wear in a male’s presence. Changing in the bathroom wouldn’t be much of an inconvience either. In fact, the only negatives at all were the fact that I wouldn’t feel comfortable taking off my bra to sleep or lounge around the room and a slight tickle in the back of my mind that I might have been able to have fun if I were all alone at a hotel a long way from where anyone knew me.

That last actually argued for having Ron with me because I knew that I shouldn’t give into temptation. Besides, I knew that he was in much the same situation regarding finances, and it wasn’t like we hadn’t stayed in the same room before, though it was never just the two of us.

After I considered all the factors, the doubts that my coworkers had created pretty much evaporated during the drive, and I warmly greeted Ron with a hug when I reached the room.

By Saturday afternoon, I was glad that I hadn’t let them get to me. There had been no problems at all, and both he and I were having a great time. We were, however, exhausted.

Several nights of staying up late talking coupled with early morning meetings add up after a few days. We decided to skip the afternoon round of sessions and take a nap before the big banquet. As I woke up, glancing at Ron gently snoring in the next bed, I discovered that we had overslept, and there was no way we’d make the dinner on time.

“Ron, wake up. We’re seriously late!”

“Huh? What?”

“We should have left a half hour ago. What should we do?”

Ron rubbed his eyes and picked up the clock from the nightstand.

“Well, I say we skip it. I hate all the boring speeches anyway.”

I agreed with him. Missing it wasn’t that big of a deal.

“Do you want to go back to sleep?”

“Nah. It’s after seven as it is. If I sleep any longer, I wake up at midnight and be up the rest of the night.”

“True that. Anything you want to do?”

He got up and walked over to his bag, reached in, and pulled out a battered paperback copy of The Book of Questions.

I smiled.

“Good idea. It’s been a while. You want to start?”

He opened the publication randomly and began asking away. There were no set rules as to a predetermined number of questions that one person could pose before yielding. We followed conversations to their natural conclusion and then went on to the next topic. The only hard and fast standard for the game was that you had to answer truthfully.

We had alternated roles many times in a couple of hours when I handed the book back to him. Instead of looking inside it, however, he paused, looking pensive.

Then, staring straight into my eyes, he asked, “exhibitionist or voyeur?”

This was new. We had never touched on anything remotely sexual. Without thinking, I answered, perhaps a little too quickly.

“Exhibitionist.”

He didn’t pause.

“From your clothing, I wouldn’t have thought that you would say that. Why do you dress so conservatively?”

“I think that it depends on what you mean by exhibitionist. If you mean these little teeny boppers who go to the mall in short shorts and tight shirts, then that’s not me. If you mean someone who finds being seen, uh, less than fully dressed as, uh…”

“Exciting,” he said.

“Yeah, exciting. Then that’s what I am.”

I don’t know that I had ever even admitted that to myself.

“How many guys know what you look like without any clothes since you reached puberty?”

That was an oddly phrased question. What was he getting at?

“I don’t know.”

“Explain.”

I blushed.

“Two boyfriends have actually seen me naked, but there may be more who have seen pictures. I don’t know.”

“Why would you think that others may have seen photos of you?”

His questions were coming fast. I couldn’t tell what he was feeling. Anger? Determination?

“This is really embarrassing.”

His demeanor softened, and I started with my answer before he could say anything.

“You remember Alvin?”

He nodded.

“A couple of months before we broke up, he asked if he could take some pictures of me. I could feel the relationship slipping away and, stupidly, thought that giving him what he wanted would make him stay with me.”I couldn’t believe that I was telling anyone this, especially not Ron, but, once I started, I couldn’t stop.

“I wasn’t worried about anyone walking in on us because his roommates were out of town that weekend, but it still felt funny getting undressed in the living room. By the time I finished, I was so nervous that I was shaking. I mean, I’m not pure as the driven snow or anything, and he had definitely SEEN me before. It’s different, you know, when it’s in bed, and neither of us are wearing anything. This was me standing there while he looked at me.

“That first set was just a few pictures. He took one of me from the front, one from the side, and one from the back and that was it.”

“What happened next?”

I glared at him.

“What do you think happened?”

He grinned.

“Did it, uh, enhance things?”

Just when I thought that I couldn’t blush any deeper, I did.

I couldn’t speak. I just nodded.

“Did he ask you for more pictures?”
“Yes, three more times.”

“Did you agree?”

A simple yes would have answered the question. I don’t know why I continued as I did.

“For the second session a week or so later, he had me pose on the bed. At first, it wasn’t too bad. He had already taken pictures of me, and this was at least in the bedroom. Then he said something about taking it from Playboy to Hustler.”

I couldn’t look at him. Instead, I stared at the floor.

“He had you spread your legs?”

“Yes. And then get on my hands and knees. It was degrading and humiliating, but also…”

“Exciting.”

I nodded.

“Afterward was really, really good, so I didn’t mind as much a couple of weeks later when he asked again. This time, he had a blindfold and ropes.”

I didn’t feel the need to elaborate.

“The final time was less than a week before we broke up.”

“Was that time bad for you?”

“Very. Afterward, I couldn’t believe how far I went. He had me, you know, touch myself.”

“Did you break it off or did he?”
“He did.”

Ron shook his head.

“So,” he said, “you answered before that you didn’t know how many guys might have seen you…”

“Yeah. I don’t know if he’s shown those to his friends, or around school, or where.”

“How do you feel about that?”

“It’s embarrassing. Sometimes I’ll think that a guy is looking at me, and I wonder if he’s seen me naked. On the other hand, sometimes, when I think about it, it makes me a little, uh, excited.”

“Before the pictures, had you ever realized that you liked the thought of guys looking at you?”

I shook my head.

“Have you done anything exhibitionist since?”
Telling about the pictures was one thing. I mean, a lot of girls have let their boyfriends photograph them. I really wished he hadn’t asked this question though.

“Yes.”

“Really? What kinds of things?”

My voice must have been really low because he had to lean forward.

“I found this Truth or Dare website and began reading some of the things that some girls have done. Recently, I’ve sort of dared myself to do things.”

He shifted in his seat.

“Wow. What things?”

I glared at him.

“Things!”

“Come on. Please? Don’t leave me hanging.”

“The first dare was really tame. I dared myself to spend all evening naked.”

“That’s it?”

“Yeah. That’s it. It’s not exactly like I ever am naked anywhere but my shower usually. So I found sitting around my apartment without clothes exciting. Okay?”

“Did anyone see you?”

“NO! I made sure all blinds were closed the whole time.”

“How long did you spend nude?”
“From the time I got home from work until I woke up the next morning.”

He started to ask another question, but I started talking before he could.

“The next time, I dared myself to stand outside my apartment for five minutes.”

“Fully naked?”

“Yes.”

“Did you do it?”

“Yes.”

I could tell that he was dying to ask me about the experience, but I wasn’t going to volunteer anything or talk about what I did after my dares.

“The third and final time was last weekend. I waited up until 3am on Friday night and dared myself to go get my mail.”

“You took off all your clothes, climbed down the stairs from the third floor, and walked across your parking lot? I don’t believe it.”

“I did. I was shaking like a leaf the whole time and cursing myself six ways to Sunday for being an idiot, but I did it.”

“Did you enjoy it?”

“I don’t know. It was terrifying, and I have no idea what I would have done if someone saw me. I think I’d have to move if that happened. On the other hand, it was the most exciting thing I had ever done.”

“Are you going to do more dares?”

“I don’t know. I know that I shouldn’t. It’s stupid and dangerous, but I don’t know if I can stop. After my second dare, I told myself that that was the last time…”

“I’m cringing at the thought of you meeting some guy while you’re doing this. You could get seriously hurt.”

“I know. I said it’s stupid and dangerous. I still can’t believe that I was out in public for like 30 minutes naked.”

“It took you 30 minutes to get your mail?”

“Yeah. It takes a long time when you’re stopping and making sure you don’t see or hear anyone around every few seconds. And I didn’t wait to get back to my apartment before…”

I clamped my head over my mouth.

He grinned.

“Well, this has been an enlightening conversation. I brought up the whole thing because I have something that I need to tell you. I had no idea how to bring it up, though, and I figured I’d try to feel you out to see if you already knew. It doesn’t sound like you do, though.”

I had no idea what he was talking about, and I was too shocked at my own revelations to him to think much about it while he got up, got his laptop, and brought it back over to me.

With the computer facing away from me, he began typing and clicking the mouse. Finally, he turned it to where I could see the screen. There, filling the screen in full color, was an frontal view of a very naked me standing in Alvin’s living room.

My mind went blank as I reached out for the mouse. Scrolling down the thread, I found picture after picture of me showing my most intimate parts. When I got to the end of the first page, not bothering to read any of the comments, I used the slide bar to move the page back to the top. The thread was started by “thechipmunk” the day after Alvin first had me pose for him!

The second page of the thread started with me bound spread eagle on his bed and continued with images of me rubbing my breasts, pinching my nipples, massaging my clit, and sticking my finger inside myself. The very last post before the comments started contained a file. Horrified, I clicked on it.

A screen opened up and began playing. A figure that I very quickly realized was me was busy bringing herself to orgasm while moaning quite loudly.

I didn’t even know that his camera could take video!

Suddenly, I realized that Ron was standing beside me looking over my shoulder.

“Oh my God!”

I hastily closed the video and the browser. In retrospect, it was a bit silly. Obviously, he had already seen everything. Still, I couldn’t sit there looking at naked pictures of myself with a guy there.

“How many?”

I don’t know how he understood that I was asking how many guys had seen this thread, but he did.

“Hard to say. A lot. Thousands.”

Thousands of guys had not only seen my intimate places but had seen a video of me doing the most private thing that I do!

“If it’s any consolation, this site puts a bookmark on all photos that are posted, so they don’t really spread around the Internet,” he said.

“Great. It’s limited to the THOUSANDS of guys who have already seen me!”

I was horrified. Anyone at all could have seen this. My boss could go home at night and pull this up. My clients. Anyone.

I couldn’t help but think of all those strangers looking at my totally exposed body, and I couldn’t believe how excited it made me feel.

Glancing at Ron, I noticed that he was staring at my chest. Looking down quickly, I discovered that my nipples were sticking through my thick pajama top and sturdy bra to make two sharp points.

I had no idea what to do. It felt silly to clutch my hands across my boobs; he had already seen enough pictures of me that pokies were the least of my embarrassment. Part of me wanted to crawl into bed, pull the covers over my head, and hide for the rest of my life. The other half of me wanted to run to the bathroom, pull down my bottoms and panties, and go to town on myself.

Instead, I sat there, speechless.

“The way I see it,” Ron said, “you can either run from it or embrace it.”

It struck my as funny how he, in a way mirrored my thoughts. I didn’t laugh though.

“How do I run from it?”
“Well, even though a lot of people have seen it, they aren’t that many as a percentage of the people in the world. You can email the site and ask them to remove the post. Then you can change your haircut or whatever. Unless someone really knows you, they won’t connect some website post to you.”

That made sense.

“How would I embrace it?”

“Add to the thread.”

I was stunned at his suggestion. All I could think of to say was “who would take the pictures?”

“I can. I have my camera with me.”

“Who would want to even look at me like that? It’s not like Hugh Hefner is going to be calling me up or anything. I’m 23 years old and already my breasts are sagging, my stomach is too big, and have you seen how thick my thighs are?”

“A lot of people wanted to look at you. You can tell by all the posts that this thread was very popular when it was active. Heck, look at all the requests for updates since the last one.

“Personally, I think about the most titillating thing in the world is a girl who is obviously shy but also very obviously turned own by showing off. That’s you in spades.”

“But I don’t want that kind of relationship with you. I mean, I can’t see us dating as it might ruin the friendship, and I’m not into the friends with benefits thing.”

“We don’t have to do anything physical. In fact, I promise that I won’t touch you at all inappropriately no matter what happens tonight. Think of it this way, you’ll have friend who can help you and keep you safe.”

When I didn’t respond, I’m sure that he knew he had me.

“Gina,” he said, “I dare you to take off your clothes.”

I was standing with my thumbs inside the waistband of my pajama bottoms before I even thought about what I was doing. I hesitated a moment at that point, considering whether I wanted to go through with it. I know that he had seen images of me naked, but actually having me strip in front of him is a whole different ballgame and would change things between us forever.

Ron pulled out his camera and took a picture of me in that position.

I eased the pants down over my butt and thighs before releasing them to fall to the floor. Wordlessly, I stepped out of them. The tails of the shirt covered my plain, white panties, but he whistled anyway.

“There’s almost nothing in this world sexier than a woman wearing just a top, the anticipation of seeing even more. Wow!” he said as his camera shutter snapped once again.

Each button of my blouse that I unfastened led to another set of digital bytes that would immortalize my exposed body.

As the flashes continued to freeze my figure in time, I slowly opened the top to expose my 34DD bra encased breasts and my embarrassingly old lady like panties. I didn’t let my increasing mortification stop me, though. Instead, I pulled the garment back over my shoulders and let it fall to lay on the floor next to the discarded bottoms.

“Lean forward,” he said.

I complied, letting him photograph my enormous cleavage.

“Turn around.”

I straightened up and pivoted, coming to rest facing away from him.

I could hear the camera’s shutter and see the flashes of light.

“Unlatch the bra.”

I reached up and undid each of the four catches in succession, knowing that each tiny movement was being recorded for posterity.

Once the strap separated, he had me turn back toward him. He took more pictures of me standing there, arms at my side, with my bra loosened by still not quite exposing my rock hard nipples.

“Lean forward.”

Without looking down, I knew that my areola must be showing, and Ron certainly wasn’t failing to document the moment thoroughly.

“Okay. You can straighten back up and then lose the bra.”

As I shrugged the straps off my shoulders and let the piece of clothing fall, a moment of extreme modesty overcame me. Though he now surely had multiple photographs of my bare boobs, I covered them tightly with my hands. Surprisingly, he seemed to like that and continued to snap away.

“Now lower your arms but keep them across your stomach.”

This instruction was even harder to follow than taking off the bra in the first place. It was like his words overpowered my brain, though, because I did as I was told.

“All the way to your sides,” he said after several snaps.

I dropped my hands to nervously clutch my thighs, completely revealing my whole stomach and chest to him. The only covering for my entire body was the simple, thin fabric, now soaking wet, protecting my nether regions.

I couldn’t look at him or the camera, as it recorded my embarrassment.

“Turn again.”

I did.

“Bend from your waist as you drop the panties. Don’t rise until I tell you to.”

I slowly pushed the white fabric down, exposing more and more of my pale butt flesh and crack as I leaned over. Soon, only the part between my clenched legs was offering any resistance, and even that small portion eventually yielded to the constant downward pressure. The garment then dropped to rest at my ankles.

“Staying in the same position, kick off the panties.”

I’m not exactly athletic or graceful, and it took some contorting to perform this feat, especially while trying to keep my thighs clamped as tightly as possible. The relentless camera continued to catalog each second until I was finally able to remove them completely.

I was now completely butt naked in front of Ron! Nothing at all covered the tiniest part of me.

“Put as much of your hands on the floor as possible.”

I stretched until the tips of all five fingers were in contact with the cheap gray carpet.

“Separate your feet until you are able to reach your entire palm onto the floor.”

For the first time since this started, I didn’t immediately comply. I knew exactly what parts of me such movement would show, and I couldn’t move. I couldn’t refuse his command, either, so I remained in that bent over position expecting him to either insist that I obey or to relent.

Instead, he did nothing.

For once, the camera was silent, and no explosions of concentrated light illuminated the room.

The silence stretched on and on.

Finally, I couldn’t take it any longer, and I slowly began sliding my feet apart. As soon as I began moving, the snapping and flashes resumed, and I knew that my most private girl parts were once again being digitally stored for anyone in the world to see.

My nipples ached painfully at the thought of millions of guys looking at me in my current pose, and I could feel my juices trickling down my leg.

It wasn’t long before he told me to stand up and face him once more. As I stood there, my full frontal nudity on display to him and his camera, my arms behind my back and nothing whatsoever covering the thick brown curls of my pubic hair or my enormous sagging breasts, I couldn’t help but giggle.

“What’s funny?”

“I was just thinking. I’ve heard in several movies about guys thinking with their small head instead of their big one. Even though I don’t have a small head, I think that I’m thinking with one.”

He laughed too.

“Well,” Ron said, “whichever head you’re thinking with, I’m glad you completed your first dare. For your second one, I think it’s time to eat.”

The first thought that entered my mind made me shiver in excitement before I remembered that he had promised not to touch me. Damn.

He walked over to his bed and sat beside the nightstand. After quickly looking something up in the phonebook, he picked up the telephone and dialed.

I heard him say “One large pepperoni pizza” before giving them his credit card info and telling them our motel and room number.

Then the concepts of dare, eat, and pizza delivery coalesced in my mind.

“You’re not going to make me answer the door naked, are you?”

Instead of answering, he retrieved his laptop and motioned for me to sit next to him.

When I had done dares by myself, my own touch had been enough to keep me satisfied. Being naked in a room with a guy, despite my protestations about our relationship earlier, made me crave contact from him, so I sat closer to him than I needed to. The feel of his shirt and shorts, and the bare leg, against my unprotected skin sent shivers through my body.

He opened up a video that he had saved on his hard drive. It showed a very large woman answering the door wearing only a towel. As she reached out to hand the pizza guy her money, the towel slipped to the floor. She made a small attempt to hide behind the door but mostly let the man look at her. He seemed more embarrassed than she did.

I sat speechless. I don’t know what it is, exactly, about watching porn with a guy while completely nude that makes it so hard to keep from touching yourself, but I had to literally put my right hand under my thigh because it keep drifting to places where it shouldn’t.

“That’s the easiest form of the dare as you can pretend it’s an accident,” Ron said.

He pulled up another video. This one showed a slender, apparently college aged girl walking butt naked up to the door. She opened it wide and pranced around unembarrassed in front of the delivery guy.

After seeing this girl show herself off to a stranger for a good two minutes straight, it was all that I could do to leave my hand in place. I wonder if Ron noticed me clutching the bedspread?

“That’s the other common form, pretending like it’s nothing out of the ordinary. My preference is a third type.”

The final video showed a girl whose shirt barely covered her naked bottom inviting the guy into her house. As he watched, she laid down on a bed, legs spread wide, and pulled up her shirt to just under her chin.

This one proved to be too much for me, and I couldn’t help but stroking my clit a little. I tried to be as unobtrusive as possible, but it’s not like there was anything hiding what I was doing.

“I think that having to strip in front of the man makes it so much hotter. Your dare is this: when you hear the knock on the door, put on your panties. Open the door, and invite him into the room. After you give him the get the pizza from him, tell him that, for his tip, he can either have $5 or your panties. At each step, you also have to pose for pictures.”

I couldn’t believe it. He was guaranteeing that someone else would see me naked, not just on the Internet, but in person. I was so far gone by then, I simply nodded as low moans escaped from my throat.

“Oh crap!” he said.

His voice was so loud that it broke me from my haze, and I hastily moved my hand away scared that he was shouting about the fact that I was about to start full on masturbating while sitting beside him.

Instead of commenting on my wanton behavior, he said “I completely forgot to order drinks. I guess I’ll just have to dare you to go get some.”

He stood up, motioning for me to follow suit, and once again grabbed the camera.

I was still a little shaky from my mini orgasm, but, wobbling only slightly, I did as he said.

After digging around in his suitcase, he handed me a fist full of change.

“I dare you to go down to the first floor and get a Coke for me and something to drink for you as well. You have to go as you are now, not even putting on shoes, and you cannot cover yourself in any way for any reason.”

“What will you be doing?”

He simply raised up the camera and grinned.

If you asked me if taking off your clothes the first time in front of a guy or stepping naked from inside to outside where anyone might be able to see you were more difficult, I wouldn’t be able to answer you. Both are bad exciting in different ways. In the first case, someone is definitely going to see you, but your exposure is limited to just that person. For the later, anyone at all could see you. The police could come. Anything could happen.

As I opened the door to peek out, the flash went off behind me. I did my best to ignore it as I concentrated intently on my surroundings.

The walkway in front of our room was open to the parking lot, but it was on the backside of the motel. Luckily, we were located on the back half of the building, so only people staying in this block rooms would have any cause to come back here. The parking lot, even with both Ron’s car and mine, looked only about a quarter full. The problem was that it was only 9pm, hardly late enough to limit people being out and about. I couldn’t see or hear anyone, though, so I hesitantly, trying to make as little noise as possible, stepped outside the door.

As it had on my two previous exterior adventures, my senses seemed heightened. I could feel the warm night air on every part of my body, and noted with distracted interest that, though it heated most of my skin, it felt cool on my exposed sex. The rough finished concrete didn’t hurt much, but it did enhance my awareness of my vulnerability knowing that not even my feet were protected.

Moving only far enough away to let Ron out behind me, I stopped and listened. I could hear the TV a couple of spots down, CSI Miami it sounded like, but the two rooms between me and the stairs were dark and quiet.

Still I hoped that Ron didn’t decide to take a picture as the flash would be sure to draw attention if anyone were nearby. For a wonder, he didn’t.

Slowly, I tiptoed to the corridor dividing the building in two halves. Clutching the edge of the brick façade, I peered at the opening. Though no one was currently there, I could see cars passing on the frontage road.

I looked back at Ron and saw no mercy in his expression. Sucking in my breath, I dashed across the gap to the top of the open stairs. I was halfway to the ground floor when I heard him call out.

“Hold up for a second. Turn around.”

Knowing what was coming, I stopped and posed for him, wincing as the flash seemed to light up the entire world. I was sure that every person in the hotel couldn’t help but be aware of what just happened.

After two shots, he motioned for me to proceed, and I continued carefully the rest of the way down, listening intently after every step. The vending machines were located in a room at the bottom of the stairs, and I slipped quickly in as soon as I ascertained that it was unoccupied.

Ron snapped away as I fed quarters into the machine, as I made my selections, and, especially, as I bent to retrieve the beverages.

Now burdened with a cold drink in both hands, I stuck my head out into the corridor and looked both ways before dashing back up the stairs. This time, instead of creeping carefully, I ran the whole way.

As I reached the door mere moments later, I twisted the knob, but nothing happened. The door was locked.

All I could do was wait, naked and vulnerable, for Ron to come open it.

“You do have the key, don’t you?” I asked as he sauntered towards me.

“Of course.”

“Can you please open it?”

“In a second. First let me just get a shot or two of you trying in vain to do it yourself.”

He posed me with both my hands tugging on the door, the drinks hidden out of sight of the viewfinder. After two quick snaps, he quickly grabbed the bottles and opened the door. I swear that I heard someone undoing a safety chain in the room with CSI playing as I darted inside.

My heart was pounding as I threw myself on the bed.

“Exciting enough for you?”

I could only glare at him. He was right, though, I was terribly excited.

As I valiantly struggled to keep my hands away from doing something that shouldn’t be done in polite company, Ron pulled the card from his camera and put it in the computer.

“What are you doing?”
“Getting the pictures ready to upload to the site. I figured I’d post a set of you stripping tonight and then wait a couple of days before following that up with getting the sodas. Want to help?” he said.

It was weird in the extreme to sit on the bed, totally naked, next to a fully clothed guy while helping him choose the most erotic nude images of yourself. I was certainly no less aroused when the knock on the door came than I was when we began.

To be honest, I had gotten engrossed in the project and had forgotten about the pizza. While I went into a state of blind panic, Ron grabbed my panties of the floor and handed them to me. For some reason, his touching my underwear like that sent a new wave of embarrassment through my body.

As quick as I could, I pulled the garment up to my waist while Ron got in position to record the upcoming dare. My heart pounding furiously, I walked to the door and, standing behind it, pulled it open. I placed just my head around it to see the young, red shirted delivery guy.

I heard a shaky voice barely recognizable as my own invite him in.

His eyes widened as he entered the room and caught sight of me, and I all but slammed the door behind him. I had to fight hard to not cover my exposed breasts as the expression on his face turned into a smirk.

“Um, this order was put on a credit card for a Ron Applewhite? I need a signature?” he said.

“That would be me,” Ron said, walked across the room to take the receipt and sign it.

Once he had completed the paperwork, leaving no tip, he turned to the guy.

“Would you mind if I took a couple of pictures of you with my friend?”

“Sure. No problem.”

The guy beamed a big smile and draped his arm around my bare shoulders. After a couple of shots, he asked Ron, “can I, uh, touch anything else?”

“No, I don’t think that would be a good idea. However, we did have an idea for a tip. Gina?”

It was time for me to try to find my voice.

I picked up my wallet from the table.

“You have a choice. You can either have $10…”

I tried the best I could to implore him with my eyes to take the money, ignoring the glare from Ron at the offer of twice as much cash.

“Or you can have my panties.”

He didn’t miss a beat.

“The panties.”

I just knew that he was going to say that!

Was I really going to do this? Let ANOTHER guy see me in my all together?

I hooked my thumbs under the white fabric at my waist and pulled outward slightly. Slowly, I pushed downward, and, inch by inch, revealed my brown curls to a total stranger with Ron snapping away the whole time. I felt like, by now, mine was the most well documented bush in the world.

With my entire hairy triangle fully exposed, there was no reason to extend my torture. Figuring it was best to get it over with quickly, I forced the garment past my thighs and let it drop to the floor.

Ron stopped me from immediately kicking them off.

“Wait a sec. Let’s get a shot of him with you with the panties around your ankles.”

Somehow, I think that having them on me but not covering anything actually heightened my humiliation and excitement.

The guy put his arm around my shoulder again and posed.

“Okay,” Ron said, “Go head and drop them on the floor.”

I did so, and he took another picture, this one of me standing totally, 100%, completely naked with a strange guy’s arm embracing me. At least he wasn’t trying to cop feels are anything.

“Both of you walk forward two steps.”

We did as Ron backed away from us.

“Gina, turn around please.”

I positioned myself so that both of them could now look at my bare ass.

“Now bend over and pick up the panties.”
This pose seemed to be one of Ron’s favorites. I don’t know why I did it, usually I waited for him to dare me to do something before doing it, but this time I didn’t wait for instruction. Instead of grabbing them and standing right back up, I stayed in that position and spread my legs.

I knew that the pizza delivery man could see absolutely everything, but I was too excited to care. I could feel him moving all around me; I even imagined, maybe, his breath on my most private place. As flash after flash went off, I remained there, panting, with my huge breasts dangling almost down to the carpet and my intimate areas in full view.

It seemed like an eternity before Ron spoke again.

“You can stand now.”

Both he and the pizza guy looked flushed, but I’m positive that my degree of embarrassment topped theirs by a substantial margin. I can barely even remember Ron telling the other man to go. I had been naked for almost an hour doing all sorts of kinky dares, and all I wanted was to relieve the pent up pressure.

“Ron, I really, really need some privacy right now. Would you mind leaving for a little while?”

Instead, he grinned at me.

“Gina, I dare you to let me watch.”

By this point, I didn’t care. I laid down on my back on top of the bedspread with my legs spread and my feet flat behind my thighs and began caressing my breasts as he once again started taking pictures. The thought that thousands of guys would be viewing this scene only increased my desire.

After all the buildup, I skipped most of my usual preliminary routine and moved quickly from teasing my nipples to massaging my clit. It didn’t take long for me to reach a small climax, but I wanted more, much more.

Switching to my left hand to give attention to my engorged slit, I stuck two fingers in my gaping hole. In and out, I thrusted hard while arching my back off the bed to get better access.

I felt the sensation building and quickened my pace. Soon, I came. Hard. I clutched the sheets with my hands to try to stop my limbs from quivering as waves and waves of pleasure shot through my body.

Strangely, though, as the after effects of one of my biggest orgasms ever wore off, I realized that my needs were not sated. Something was missing. I looked at Ron and realized that I wanted him inside me.

My eyes met his, and I whispered “please?”

“I can’t; I promised.”

I whimpered.

“But I NEED you.”

“Sorry.”

I nearly started crying.

He went to the other side of the bed and pulled back the covers, motioning me towards him. I rolled over onto the sheet.

He covered me up and went to turn off the lights.

In the darkness, I expected to hear him settle into his bed. Instead, I felt the covers on the side next to me move, and he climbed in next to me. I fell asleep with his arm around me.

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Billy Makes a Wish

“Shhh, did you hear that?” Billy asked.

“I keep telling you; there’s no one here. My parents won’t be home for another hour. Now, turn the page,” Mike said.

“Ahh, Ms. December, in all her glory. Damn, she’s fine. I’m really glad that you found your dad’s stash of Playboys, Mike, and they’re so current!”

“I do rock, don’t I?”

“You know what would really rock? Seeing a real girl nude. Too bad there’s no way for that to happen.”

At fourteen, a year older than Billy, Mike was the leader and idea man of their two man crew, and, when he put his mind to something, he usually was able to pull it off.

“No way, huh? I was just thinking, you know that new babysitter that my mom hired to look after my little sister…”

******

Jennifer knew that he dad wanted a particular Craftsman drill bit set for Christmas and had desperately tried to figure out how she was going to earn the $100 necessary to buy it for him. He did so much for her, paying for her clothes and anything that she needed, that is was a matter of pride for her to earn the money herself to pay for his gift. Since she didn’t have a car yet, the sixteen year old wasn’t able to even get seasonal employment at the mall. Luckily, she found out that a family a couple of blocks away needed a babysitter.

Her first session last weekend had went well, and she made sure to show up on time the next Friday night. When she arrived, the elder Hendersons had already left, and the son, Mike, was sitting on the couch in the living room.

“Hey, Jen. The rents had to leave a little early, so I agreed to keep an eye on Carol until you got here.”

Jennifer had met the boy only briefly last week as he had pretty much taken off right after shaking her hand. Still, he had seemed nice enough.

“Cool. Where is she?”

“Upstairs.”

She couldn’t help but notice that Mike appeared to be depressed.

“I don’t mean to intrude, but are you okay? You look a little down.”

“Oh, it’s nothing, just dealing with Billy.”

“Billy?”

“My best friend. No one told you about him? He’s got cancer and isn’t expected to live much longer.”

“Oh my gosh! How horrible. No wonder you’re upset.”

“Yeah, it’s tough, but I’ve mostly come to terms with it. We’ve known for a while…”

Mike turned away from her and wiped his eyes.

“Anyway,” he said, facing her again, “the real problem is the Make a Wish Foundation. They denied his request.”

“That’s terrible. I’m sure that their resources are quite limited, though. Surely, they would grant it if they could.”

“It’s not that hard! I mean, he’s dying, and it’s CHRISTMAS. They could if they wanted to!”

He turned away from her for a second time. He took several deep breaths before looking at her again.

“I’m sorry. It’s not your fault,” he said.

“What did he want?”

Mike looked at the floor before speaking.

“I’m a little embarrassed.”

“It’s okay, just tell me.”

“You won’t laugh or be mad?”

“I promise. I won’t laugh or be mad.”

“Well, he’s a great guy. I hope that this doesn’t make you think poorly of him, but he really wants to see a naked girl before he dies.”

“Oh!”

Jennifer was a little shocked, but she guessed that she could understand. Boys were naturally curious about such things.

“Can’t you get him a magazine, or a movie, or something?”

“He’s seen girls in magazines and stuff. He’s wants to see a real live girl before he dies, and I don’t know what to do about it.”

Jennifer didn’t know what to say.

“How about you?” Mike asked. “Would you do it?”

She was stunned. She’d never even had a boyfriend. No one had seen her naked since she was a small child.

“I don’t know…”

“C’mon, please. He’s DYING!”

Jennifer couldn’t help but think of those heart wrenching advertisements asking you to support St. Jude’s. All those little kids sick in hospital beds made her cry every time. How could she not grant a dying boy his last request, but, on the other hand, how could she do it?

“Completely naked?”

*****

Jennifer couldn’t believe that she was doing this. She put a long coat on over her Pep Squad uniform – Mike had wanted her to wear a cheerleader outfit, but this was the closest thing that she had – and walked over to Billy’s house. His parents were apparently away for the afternoon leaving the sick boy in his best friend’s hands. She couldn’t imagine how hard that it must be on them, knowing that they’re about to lose their only child soon.

Her hands trembled a bit as she rang the doorbell. Mike answered let her in and escorted her upstairs to a bedroom. He introduced her to Billy, who lay under covers and had a baseball cap on his head. He looked just like those kids on the commercials.

“Nice to meet you, Billy,” she said.

“Nice to meet you too. Thank you so much for doing this.”

His voice was so soft and weak.

“Well, if Mike will leave the room, we can get started,” she said.

“Please, can Mike stay? This is really embarrassing, and it would be so much better if he were here with me. You know, for support.”

Jennifer couldn’t believe that he was complaining about being embarrassed. He wasn’t the one who was taking his clothes off. Besides, it was one thing to be getting naked in front of someone who was about to die. It was quite another to strip in front of someone who she’d see again. Still, could she really say no? He was about to die.

She couldn’t look him in the eyes.

“Okay.”

She took off her coat, folded it, and put it over a chair in the corner. She then closed the door; it wouldn’t do to have his parents come home early and discover what was going on.

She stood in front of the two boys wearing her red and blue striped sleeveless top with “Rebels” emblazoned across it, a short pleated skirt, bloomers, her underwear, white ankle socks, and shoes.

What should she do now? Start stripping? Turn on music?

“Are you wearing those things that cheerleaders wear over their panties?” Mike asked.

She nodded her head.

“Would you take those off first?”

Blushing, she figured it was as good a place to start as any. She reached under the skirt, slipped the red bloomers down her legs, and stepped out of them.

“Can we see your panties?”

Jennifer held the skirt up revealing lacy white panties, her sexiest pair.

This time it was Billy who spoke.

“Would you mind turning around?”

Her face enflamed even more as she, while still holding her skirt high, turned in a complete circle so that they could see her panty clad behind.

“How about the top next?” Mike asked.

Billy nodded.

Fixing her stare at a spot on the carpet, she grabbed the bottom of her shirt and pulled slowly up, exposing first the pale flesh of her taut stomach, then her belly button, then the outline of her ribs. She paused to gather her courage when the material reached the bottom of her bra.

In a rush, she finished pulling the garment off, exposing her full C-cups encased in a lacy white bra to the adolescents.

The boys seemed mesmerized at the site of her less than decently covered breasts, and, for several moments, no one spoke. She stood there, hands by her side, letting them look.

“What next?” she finally asked.

Mike’s voice squeaked.

“Your bra?”

She turned her back to them. It seemed to her that it took forever for her shaking hands to undo the three latches holding the foundation garment together. She then shrugged the straps off her shoulders and let it fall to the floor. She couldn’t help but clutch her hands over her boobs and was surprised to discover exactly how hard her nipples were as they made indentations in her palms.

Wishing that she were anywhere but here, she turned to face them. Before one of them could summon up the courage to ask her to, she lowered her hands. Not daring to look up at them, she stood there, waiting.

It must have been five minutes before Mike spoke.

He cleared his throat.

“Could you take off your panties?”

She quickly reached under her tiny skirt and gave the garment a tug. In seconds, they were pooled around her shoes, and she stepped out of them.

She was pretty sure what they wanted next, so she raised the skirt up revealing her light brown pubic hair. She stood there for a moment and then did a slow turn.

“Is that good? Can I get dressed now? You’ve seen everything.”

“Would you mind taking off the rest?”

Though embarrassed beyond belief, she couldn’t stop now. She unzipped the skirt and let it fall to her feet. She stood totally nude before them.

“There.”

“Everything please.”

She was naked. What else was left? Then she realized that they wanted her to take off her socks and shoes. She bent over.

“Would you mind turning around first?”

She did another circle for them.

“I meant, take your shoes off with your back to us.”

She blushed even more furiously as she realized what they wanted.

Jennifer always was the type that believed that anything worth doing was worth doing right. Once she was facing the wall again, she spread her legs wide and bent at the waist. She took her time slipping off both her socks and shoes.

She couldn’t help but looking back at them through her legs. The boys were completely enthralled. They weren’t even blinking.

She imagined the sight that they were seeing, her butt, exposed pussy, tits hanging down. She glanced involuntarily up and noticed fluid seeping down her thighs.

She stood up and faced the boys.

“Okay. That’s it. I’m getting dressed now.”

It was Billy who spoke up this time.

“One more wish?”

She glared at him.

“A hug?”

Even naked, it was hard to deny a kid a hug, especially a dying kid.

She walked over to the bed and put her arms around him, drawing him close. He didn’t feel nearly as frail as she would have thought. He pressed his face between her breasts, and the bill of his ballcap dug into her neck. She was about to chastise him for taking that liberty when she noticed something. The cap had risen off the back of his head, and he had hair.

She grabbed the hat and backed away.

“Oops,” Mike said, “I guess the jig is up.”

Jennifer threw her hands across her bush and breasts.

“You lied to me? He’s not really dying?”

The two boys nodded.

She grabbed her clothes and ran out of the room, quickly finding the bathroom. Sitting on the toilet with her hands covering her face, she thought, ‘I can’t believe I did that. I stripped for two boys for no reason. I revealed simply everything to them. Everything.’

She felt so stupid, so used, but she also felt very, very horny. The more she thought about her exposure, the more aroused she became. Soon, she couldn’t help it, and her hands flew to her soaking clit. It didn’t take long for her to have the most explosive orgasm of her life.

When she recovered, she got dressed and staggered back to Billy’s room.

“I’m babysitting for Carol again tomorrow night,” she said. “If you’re there between the time she goes to sleep and the time her parents get home, I have a sexy elf costume that I thing you’re going to love seeing me take off.”

Merry Christmas!

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